Benzyl (2S,3aR,7aS)-octahydroindole-2-carboxylate hydrochloride

Base Information

• Chemical Name: Benzyl (2S,3aR,7aS)-octahydroindole-2-carboxylate hydrochloride
• CAS No.: 145641-35-6
• Molecular Formula: C16H21NO2·HCl
• Molecular Weight: 295.809
• European Community (EC) Number: 474-170-3
• Mol file: 145641-35-6.mol

Synonyms:145641-35-6;Benzyl (2S,3aR,7aS)-octahydroindole-2-carboxylate hydrochloride;(2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid phenylmethyl ester hydrochloride;benzyl (2S,3aR,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-indole-2-carboxylate;hydrochloride;benzyl (2S,3aR,7aS)-octahydro-1H-indole-2-carboxylate hydrochloride;Benzyl(2beta,3alphar,7alphas)octahydrindole-2-carboxylatehydrochloride;1H-Indole-2-carboxylic acid, octahydro-, phenylmethyl ester, hydrochloride (1:1), (2S,3aR,7aS)-;EC 474-170-3;WOXVBEWLLZBVSX-DSMRVHDJSA-N;Benzyl (2S, 3aR, 7aS)-octahydro-1H-indol-2-carboxylate hydrochloride;AKOS015888103;NS00078615;EN300-266719;Benzyl (2S,3aR,7aS)-octahydroindole-2-carboxylate HCl;Benzyl(2s,3ar,7as)-octahydroindole-2-carboxylate hydrochloride;(2S,3aR,7aS)-benzyl octahydro-1H-indole-2-carboxylate hydrochloride salt

Chemical Property of Benzyl (2S,3aR,7aS)-octahydroindole-2-carboxylate hydrochloride

Chemical Property:

• Vapor Pressure: 7.32E-06mmHg at 25°C
• Boiling Point: 376.3 °C at 760 mmHg
• Flash Point: 181.4 °C
• PSA: 38.33000
• LogP: 3.78130
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 295.1339066
• Heavy Atom Count: 20
• Complexity: 312

Purity/Quality:

99% ^*data from raw suppliers

(2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylicAcidPhenylmethylEsterHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2C(C1)CC(N2)C(=O)OCC3=CC=CC=C3.Cl
• Isomeric SMILES: C1CC[C@H]2[C@H](C1)C[C@H](N2)C(=O)OCC3=CC=CC=C3.Cl
• Uses: (2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic Acid Phenylmethyl Ester Hydrochloride is an impurity of Trandolapril (T713500) which is an antihypertensive and angiotensin converting enzyme (ACE) inhibitor.

Technology Process of Benzyl (2S,3aR,7aS)-octahydroindole-2-carboxylate hydrochloride

There total 15 articles about Benzyl (2S,3aR,7aS)-octahydroindole-2-carboxylate hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.1%

(2S,3aR,7aS)-octahydro-1H-indole-2-carboxylic acid hydrochloride (144540-75-0,1004292-98-1) + benzyl alcohol (100-51-6,185532-71-2) → phenylmethyl-(2S,3aR,7aS)-octahydroindole-2-carboxylate hydrochloride (145641-35-6)

Guidance literature:

With thionyl chloride; In dichloromethane;

Reference yield:

(2S,3aR,7aS-octahydroindole)-2-carboxylic acid-benzyl ester (144540-71-6) → phenylmethyl-(2S,3aR,7aS)-octahydroindole-2-carboxylate hydrochloride (145641-35-6)

Guidance literature:

With hydrogenchloride; In acetone; at 0 - 10 ℃; for 0.333333 - 0.5h; pH=2;

Reference yield:

octahydroindole-2-carboxylic acid benzyl ester hydrochloride (82717-97-3) → phenylmethyl-(2S,3aR,7aS)-octahydroindole-2-carboxylate hydrochloride (145641-35-6)

Guidance literature:

octahydroindole-2-carboxylic acid benzyl ester hydrochloride; With sodium hydroxide; In water; for 1h;

With O,O'-dibenzoyl-L-tartaric acid; In methanol; for 1h; Resolution of racemate;

With hydrogenchloride; sodium hydroxide; more than 3 stages;

upstream raw materials:

octahydroindole-2-carboxylic acid benzyl ester hydrochloride

(2S,3aR,7aS-octahydroindole)-2-carboxylic acid-benzyl ester

(2S,3aR,7aS)-octahydro-1H-indole-2-carboxylic acid hydrochloride

benzyl alcohol

Downstream raw materials:

trandolapril benzyl ester

trandolapril